Tipranavir

Chemical compound From Wikipedia, the free encyclopedia

Tipranavir (TPV), or tipranavir disodium, is a nonpeptidic protease inhibitor (PI) manufactured by Boehringer Ingelheim under the trade name Aptivus /ˈæptɪvəs/ AP-tiv-əs. It is administered with ritonavir in combination therapy to treat HIV infection.[citation needed]

Pronunciation/tɪpˈrænəvɪər/
tip-RAN-ə-veer
Trade namesAptivus
AHFS/Drugs.comMonograph
MedlinePlusa606009
Quick facts Clinical data, Pronunciation ...
Tipranavir
Clinical data
Pronunciation/tɪpˈrænəvɪər/
tip-RAN-ə-veer
Trade namesAptivus
AHFS/Drugs.comMonograph
MedlinePlusa606009
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth (soft capsules)
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding99.9%
MetabolismLiver
Elimination half-life4.8–6 hours
ExcretionFeces (82.3%), urine (4.4%)
Identifiers
  • N-{3-[(1R)-1-[(2R)-6-hydroxy-4-oxo-2-(2-phenylethyl)-2-propyl-3,4-dihydro-2H-pyran-5-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.158.066 Edit this at Wikidata
Chemical and physical data
FormulaC31H33F3N2O5S
Molar mass602.67 g·mol−1
3D model (JSmol)
  • CCC[C@]1(CC(/O)=C(\C(=O)O1)[C@H](CC)c3cccc(NS(=O)(=O)c2ccc(cn2)C(F)(F)F)c3)CCc4ccccc4
  • InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1 checkY
  • Key:SUJUHGSWHZTSEU-FYBSXPHGSA-N checkY
 ☒NcheckY (what is this?)  (verify)
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Tipranavir has the ability to inhibit the replication of viruses that are resistant to other protease inhibitors and is recommended for patients who are resistant to other treatments. Resistance to tipranavir itself seems to require multiple mutations.[2] Tipranavir was approved by the Food and Drug Administration (FDA) on June 22, 2005, and was approved for pediatric use on June 24, 2008.[3]

Tipranavir should only be taken in combination with ritonavir and other antiretroviral drugs, and is not approved for treatment-naïve patients.[1] Like lopinavir and atazanavir, it is very potent and is effective in salvage therapy for patients with drug resistance. However, side effects of tipranavir may be more severe than those of other antiretrovirals. Some side effects include intracranial hemorrhage, hepatitis, hepatic decompensation, hyperglycemia and diabetes mellitus. The drug has also been shown to cause increases in total cholesterol and triglycerides.[1]

Aptivus labeling has a black box warning regarding hepatotoxicity and intracranial hemorrhage.[1]

References

External links

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